Synthesis and properties of tetraphenylethylene derivatived diarylethene with photochromism and aggregation-induced emission

Dyes and Pigments - Tập 139 - Trang 118-128 - 2017
Huan Dong1,2, Miao Luo1, Sheng Wang1, Xiang Ma2
1Key Laboratory of Applied Chemistry and School of Chemistry and Chemical Engineering, Development Center for New Material Engineering & Technology in Universities of Guangdong, Lingnan Normal University, Zhanjiang, 524048, China
2Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China

Tài liệu tham khảo

Jin, 2016, Binding porphyrins gated dithienylethene bridge, Dyes Pigments, 132, 151, 10.1016/j.dyepig.2016.04.043 Lambruschini, 2016, Switching the photochromic activity of acenaphthylene derivatives through a tandem nucleophile-promoted addition reaction, Chem Eur J, 22, 13831, 10.1002/chem.201602912 Li, 2016, Theoretical insight into the enhanced hindrance, thermal stability and optical properties of diarylethene with a benzobis(thiadiazole) bridge and benzothiophene rings, Dyes Pigments, 125, 348, 10.1016/j.dyepig.2015.10.041 Moreno, 2016, Reversible photomodulation of electronic communication in a π-conjugated photoswitch-fluorophore molecular dyad, Chem Eur J, 22, 1070, 10.1002/chem.201503419 Yao, 2016, Recent progress in photoswitchable supramolecular self-assembling systems, Adv Opt Mater, 4, 1322, 10.1002/adom.201600281 Pu, 2016, Recent advances in diarylethene-based multi-responsive molecular switches, J Mater Chem C, 4, 3075, 10.1039/C6TC00110F Russew, 2010, Photoswitches: from molecules to materials, Adv Mater, 22, 3348, 10.1002/adma.200904102 Feng, 2008, Next step of photochromic switches?, J Mater Chem, 18, 1617, 10.1039/b713216f Tian, 2007, Photochromic bisthienylethene as multi-function switches, Chem Commun, 8, 781, 10.1039/B610004J Tian, 2004, Recent progresses on diarylethene based photochromic switches, Chem Soc Rev, 33, 85, 10.1039/b302356g Jiang, 2006, Highly fluorescent contrast for rewritable optical storage based on photochromic bisthienylethene-bridged naphthalimide dimer, Chem Mater, 18, 235, 10.1021/cm052251i Al-Atar, 2009, A photocontrolled molecular switch regulates paralysis in a living organism, J Am Chem Soc, 131, 15966, 10.1021/ja903070u Lin, 2015, Intermolecular hydrogen bonding-assisted high contrast fluorescent switch in the solid state, Dyes Pigments, 114, 33, 10.1016/j.dyepig.2014.11.001 Yao, 2014, A photochromic supramolecular polymer based on bis-p-sulfonatocalix[4]arene recognition in aqueous solution, Chem Commun, 50, 7166, 10.1039/c4cc02672a Lim, 2004, Photoswitchable organic nanoparticles and a polymer film employing multifunctional molecules with enhanced fluorescence emission and bistable photochromism, Angew Chem Int Ed, 43, 6346, 10.1002/anie.200461172 Gong, 2015, Crystallization-induced dual emission from metal- and heavy atom-free aromatic acids and esters, Chem Sci, 6, 4438, 10.1039/C5SC00253B Huang, 2016, An arch-bridge-type fluorophore for bridging the gap between aggregation-caused quenching (ACQ) and aggregation-induced emission (AIE), Chem Sci, 7, 4485, 10.1039/C6SC01254J Mukherjee, 2015, AIEE phenomenon: tetraaryl vs. triaryl pyrazoles, Chem Commun, 51, 17148, 10.1039/C5CC05973A Bu, 2015, Unusual aggregation-induced emission of a coumarin derivative as a result of the restriction of an intramolecular twisting motion, Angew Chem Int Ed, 54, 14492, 10.1002/anie.201506782 Yuan, 2012, Efficient solid emitters with aggregation-induced emission and intramolecular charge transfer characteristics: molecular design, synthesis, photophysical behaviors, and OLED application, Chem Mater, 24, 1518, 10.1021/cm300416y Zhao, 2012, Using tetraphenylethene and carbazole to create efficient luminophores with aggregation-induced emission, high thermal stability, and good hole-transporting property, J Mater Chem, 22, 4527, 10.1039/c2jm14914a Zhao, 2012, A facile and versatile approach to efficient luminescent materials for applications in organic light-emitting diodes, Chem Asian J, 7, 484, 10.1002/asia.201100753 Mei, 2015, Aggregation-induced emission: together we shine, united we soar!, Chem Rev, 115, 11718, 10.1021/acs.chemrev.5b00263 Mei, 2014, Aggregation-induced emission: the whole is more brilliant than the parts, Adv Mater, 26, 5429, 10.1002/adma.201401356 Luo, 2001, Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole, Chem Commun, 18, 1740, 10.1039/b105159h Hong, 2011, Aggregation-induced emission, Chem Soc Rev, 40, 5361, 10.1039/c1cs15113d Ou, 2016, Combined aggregation induced emission (AIE), photochromism and photoresponsive wettability in simple dichloro-substituted triphenylethylene derivatives, Chem Sci, 7, 5302, 10.1039/C6SC01205A Song, 2016, An AIE-active fluorescence turn-on bioprobe mediated by hydrogen-bonding interaction for highly sensitive detection of hydrogen peroxide and glucose, Chem Commun, 52, 10076, 10.1039/C6CC05049B Yan, 2016, An aggregation-induced emission (AIE) ratiometric fluorescent cysteine probe with an exceptionally large blue shift, RSC Adv, 6, 5636, 10.1039/C5RA22245A Zhu, 2016, Characterizing the adsorption of poly(vinyl alcohol) on colloidal silica with aggregation-induced emission fluorophore, Langmuir, 32, 2145, 10.1021/acs.langmuir.6b00288 Duan, 2016, Aggregation induced enhancement of linear and nonlinear optical emission from a hexaphenylene derivative, Adv Funct Mater Guan, 2016, Fluorescence microscopy as an alternative to electron microscopy for microscale dispersion evaluation of organic-inorganic composites, Nat Commun, 7, 11811, 10.1038/ncomms11811 Wang, 2016, A red to Near-IR fluorogen: aggregation-induced emission, large Stokes shift, high solid efficiency and application in cell-imaging, Chem Eur J, 22, 9784, 10.1002/chem.201600125 Gao, 2015, Flexible self-supporting nanofibers thin films showing reversible photochromic fluorescence, ACS Appl Mater Interfaces, 7, 9904, 10.1021/acsami.5b01996 Li, 2016, Two-component molecular cocrystals of 9-acetylanthracene with highly tunable one-/two-photon fluorescence and aggregation induced emission, J Mater Chem C, 4, 2527, 10.1039/C6TC00067C Yan, 2014, Molecular crystalline materials with tunable luminescent properties: from polymorphs to multi-component solids, Mater Horiz, 1, 46, 10.1039/C3MH00023K Shen, 2016, Recent advances of folded tetraphenylethene derivatives featuring through-space conjugation, Chin Chem Lett, 27, 1115, 10.1016/j.cclet.2016.06.031 Zhang, 2016, A series of tetraphenylethene-based benzimidazoles: syntheses, structures, aggregation-induced emission and reversible mechanochromism, RSC Adv, 6, 79871, 10.1039/C6RA16514A Zhan, 2016, Prying into the limit of CIE value for TPE-based blue AIEgens in organic light-emitting diodes, Dyes Pigments, 128, 60, 10.1016/j.dyepig.2016.01.001 Xu, 2011, Synthesis and properties of aggregation-induced emission compounds containing triphenylethene and tetraphenylethene moieties, J Phys Chem C, 115, 17574, 10.1021/jp205525s Luo, 2016, Novel organogel harnessing excited-state intramolecular proton transfer process with aggregation induced emission and photochromism, Dyes Pigments, 132, 48, 10.1016/j.dyepig.2016.04.036 Wang, 2016, New π-conjugated cyanostilbene derivatives: synthesis, characterization and aggregation-induced emission, Chin Chem Lett, 27, 1592, 10.1016/j.cclet.2016.04.020 Yao, 2014, Aggregation-induced emission encoding supramolecular polymers based on controllable sulfonatocalixarene recognition in aqueous solution, J Mater Chem C, 2, 5155, 10.1039/c4tc00503a Dou, 2011, Multistimuli-responsive benzothiadiazole-cored phenylene vinylene derivative with nanoassembly properties, Langmuir, 27, 6323, 10.1021/la200382b Seo, 2006, Lyotropic columnar liquid crystals based on polycatenar 1H-imidazole amphiphiles and their assembly into bundles at the surface of silicon, Soft Matter, 2, 886, 10.1039/b606870g Yan, 2014, Tunable two-color luminescence and host–guest energy transfer of fluorescent chromophores encapsulated in metal-organic frameworks, Sci Rep, 4, 4337, 10.1038/srep04337